Short, Enantioselective Total Synthesis of Stephacidin A

Abstract

A concise route to the heptacyclic indole alkaloid stephacidin A (1) includes a simple method for the gram-scale synthesis of substituted tryptophans, a remarkable indole annulation, and the first enolate coupling of an amide to an ester. This synthesis secures the relative configuration of the natural product and paves a potential path to several of its congeners.